Ammonia → HCID 21915108, compound

HRID 1246514Notes

Reaction equation

HRID 1246514 reaction equation
[ClH:1].[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20](=[NH:23])OC)=[CH:15][CH:14]=2)[N:10]=1)(=[O:4])[CH3:3].[Cl-].[NH4+:25].N>CCO.CO>[ClH:1].[NH2:25][C:20](=[NH:23])[CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][C:9]2[N:10]=[C:6]([NH:5][C:2](=[O:4])[CH3:3])[S:7][CH:8]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 21915039HCID 21915039, compound

Product 1

HCID 21915108HCID 21915108, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Methyl 2-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}phenyl)ethanimidoate hydrochloride (600 mg) was dissolved in EtOH (12 ml). Then ammonium chloride (136 mg) and ammonia in methanol (2 ml) were added to the solution. The reaction mixture was refluxed for 4 hours under N2 atmosphere. After cooled to r.t., the suspension was filtered in vacuo. The filtrate was concentrated in vacuo, and the residue was solidified with EtOH/diethyl ether to give N-(4-{2-[4-(2-amino-2-iminoethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide hydrochloride (338.6 mg) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours under N2 atmosphere
  2. filtrationthe suspension was filtered in vacuo
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-95656c5b3f714954bcff99f2ea6e9c6c
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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